Mevalonic acid

Base Information

• Chemical Name: Mevalonic acid
• CAS No.: 17817-88-8
• Molecular Formula: C₆H₁₂O₄
• Molecular Weight: 148.159
• DSSTox Substance ID: DTXSID801314151
• Nikkaji Number: J385.671B
• Wikipedia: Mevalonic_acid
• Wikidata: Q241678
• Metabolomics Workbench ID: 1480
• ChEMBL ID: CHEMBL1794734
• Mol file: 17817-88-8.mol

Synonyms:Acid, Mevalonic;Mevalonate;Mevalonic Acid

Chemical Property of Mevalonic acid

Chemical Property:

• PSA: 77.76000
• LogP: -0.40550
• XLogP3: -1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 148.07355886
• Heavy Atom Count: 10
• Complexity: 123

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

R-MevalonicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCO)(CC(=O)O)O
• Isomeric SMILES: C[C@@](CCO)(CC(=O)O)O
• Recent ClinicalTrials: Safety Study of MVA Smallpox Vaccine in Subjects With a History of Atopic Dermatitis (AD)
• General Description: (R)-3,5-Dihydroxy-3-methylvaleric acid, also known as (R)-mevalonic acid or mevalonate, is a key intermediate in the biosynthesis of isoprenoids and sterols. The compound can be derived from (R)-mevalonolactone, which was synthesized enantioselectively in the described study. This synthesis highlights its importance as a precursor for haptens and potential applications in analytical methods, such as radioimmunoassays, for quantifying mevalonic acid in biological samples. The compound plays a critical role in metabolic pathways, particularly in the mevalonate pathway, which is essential for cholesterol and other isoprenoid biosynthesis.

Technology Process of Mevalonic acid

There total 13 articles about Mevalonic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

mevalonolactone (674-26-0,503-48-0) → D,L-mevalonic acid (150-97-0,690-72-2,17817-88-8,32451-23-3)

Guidance literature:

With water; potassium hydroxide; at 40 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.ejmech.2014.11.040 DOI:10.1016/j.ejmech.2014.11.040

Reference yield:

→ D,L-mevalonic acid (150-97-0,690-72-2,17817-88-8,32451-23-3)

Guidance literature:

With sodium hydroxide;

DOI:10.1021/ja01566a080

Reference yield:

3-Hydroxy-3-methyl-6,6-diphenyl-hex-5-enoic acid ethyl ester → D,L-mevalonic acid (150-97-0,690-72-2,17817-88-8,32451-23-3)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH / methanol / Ambient temperature

2: (i) O₃, CH₂Cl₂, MeOH, (ii) NaBH₄, H₂O

With sodium hydroxide; In methanol;

upstream raw materials:

D,L-mevalonic acid

(R)-mevalonolactone

mevalonolactone

meglutol

Downstream raw materials:

(S)-Mevalonsaeure

5-benzoyloxy-3-hydroxy-3-methyl-valeric acid

kaurene

7β-hydroxy-(-)-kaur-16-en-19-oic acid

Refernces

A synthesis of (R)-mevalonolactone

10.1016/S0040-4020(01)88311-3

The study details an enantioselective synthesis of (R)-mevalonolactone (1) starting from (2S,3R)-epoxide 2, which was prepared with >95% enantiomeric excess (ee) by asymmetric epoxidation of nerol. The primary hydroxyl group of epoxide 2 was protected by formation of ethoxyethyl ether 5, and subsequent reduction yielded 6. Conversion of 6 to its benzyl ether 7 was followed by ozonolysis to afford intermediate 8. To remove an additional carbon from 8, it was converted to phenylselenide 9, and oxidative elimination formed an alkene, which was cleaved by further oxidation to yield alkenol 11. Oxidation of 11 with pyridinium dichromate in DMF gave 12, and reductive ozonolysis of 12 afforded benzyl ether 13. Finally, removal of the benzyl group by catalytic hydrogen transfer yielded (R)-mevalonolactone (1). The study aimed to develop a synthetic pathway that could lead to both prospective haptens and (R)-mevalonolactone from a common intermediate, with potential applications in the development of a radioimmunoassay for measuring mevalonic acid concentration in biological media.